The Physical Imposibuilitys of Brothers Winchester
by Eshlyn Kar
Summary: The way I see it the boys must have had some kind of fun so why not a book of dares. I have decided to put all of my short story's into a series. Castiel is now in the new chapter.
1. Friends

**The Physical Impossibilities of Brothers Winchester**

By: Eshlyn Kar

**Warning: may be some slight use of language**

**Chapter One**

**Friends**

Twelve year old Sam Winchester walked the halls of his school to join up with his friends. He had always kept friends up there on his list of priorities, much to the distress of Dean and their dad. If it was up to them he would have no friends what so ever, better to keep a low profile and easier to move on. But Sam was just a people person, he liked having friends.

Sam saw his small group of friends up ahead. They were a group of five, small but cozy. All of them were very friendly and had accepted him right away and didn't ask questions, which was what Sam appreciated the most. They were still at the age were girls had coodies so they kept away from the female population as much as possible.

"Hey guys!" Sam said coming up to the group. They all replied the greeting and continued talking, while making their way over to the lunch room. The sat at their usual table, eating the same usual food, while something across the room caught Sam's attention. He sat forward in his seat and rubbed his eyes in a quick motion. He didn't believe his eyes. There sitting at a table of nearly sixteen people was his brother, Dean. He seemed to be the centre of attention too, he was telling a story and everyone was listening attentively. The girls at his table were giving him shy looks and soft giggles amongst themselves, while the guys were looking at him with sheer aw. Sam had to admit, Dean looked to be pretty popular, the two words Sam never expected to come together, Dean and popular.

* * *

After school Sam shuffled his feet as he made his way to his brother's car. On his sixteenth birthday, Dean had gotten his fathers car, which was now his single most precious possession. Sam got into the impala and shoved his backpack into the back of the car. Dean was giving him a sly look and had "the grin" on. "The grin" was what Sam called the shit eating grin his brother always wore, it was a look of triumph and annoying taunting all at the same time; it drove Sam insane. 

"Hey Sam, do you mind handing me the book? It's in the glove compartment," Dean said sitting back in his seat. Sam grudgingly reached in and grabbed the leather bound book and handed it to Dean. Dean opened it to the first page and title was, The Physical Impossibilities of Brothers Winchester. It was their book of contests. How it worked was each of them wrote things in the book that they thought was physically impossible for the other to do and put in a time limit, anywhere from two days to forever depending on the challenge, and whoever did it or had the most of it by the end of the time span won. In this case, Sam had said it was physically impossible for Dean to have more friends than him with the time limit of one month. They had just started it last month after being terribly bored in the car one day.

It was the end of the month and Dean had succeeded in getting the most friends.

"Sammy let me give you a clue, the Dean always wins!"

"Yeah, whatever Dean."

Dean 1

Sam 0  


The challenge was on.


	2. Detention

**The Physical Impossibilities of Brothers Winchester**

By: Eshlyn Kar

**Warning: may be some slight use of language**

**Chapter Two**

**Detentions**

"No way dude! There is no way I'm going to do this Dean, it's so stupid!" Sam complained enthusiastically.

"Oh come on Sam it's just for one freaking week," Dean argued.

"Dean we are going to get into so much shit with this."

"Uh… that's kinda the point," Dean said with his grin firmly in place.

"No I mean with Dad. Dad is going to kill us Dean, literally kill us!" Sam tried to reason with his brother.

"Oh since when have you cared? Come on Sam just for one week, we're leaving at the end of the week anyway! Come on Sammy, please?" Dean tried to put on a begging face, but it looked more like he was constipated or turned on, Sam thought to himself with a shudder.

"Okay, but only if you promise to never ever do that face again, ever!"

"What ever you say Sammy my boy." Dean wrote the next challenge into the book:

_Who can get the most Detentions within the time span of one week._

"Dude remember it has to be only one stunt and you can't get suspended."

"Yeah yeah, I know the rules Dean."

* * *

Dean strolled towards the principal's office, with a grin on his face, which disappeared from his face very fast, because there was Sam sitting on a chair in front of the principal's office, a Kleenex in his bloody nose and an ice pack on his eye, with a big grin on his face. 

"Dude! I got a detention for the rest of the month, after school!" Sam bragged.

"What did you do?" Dean asked curiously sitting down beside his brother.

"I beat up on Bobby Matty, but I didn't get in too much trouble cause he's been bugging me for a while, all my teachers confirm it," Sam said wincing as he grabbed the ice from the seat and put it on his eye.

"I suspect you got him pretty good?"

"Haha! I broke his arm and his nose, and I'm pretty sure he won't be able to well you know for a while, I kicked where it counts pretty darn hard," Sam said smiling wickedly.

"Damn Sammy you sure know how to hurt 'em don't you?" Dean said as the door to the principal's office opened and Dean was beckoned inside.

"Well what did you do?"

"I think I went a little overboard," Dean said.

"What did you do Dean?"

"I punched my teacher in the nose," Dean whispered just before going into the office.

"Damn, I think I won."

Dean 1

Sam 1

Dean got suspended and they left town a little early so the teacher wouldn't be able to press charges.


	3. Suspension

**The Physical Impossibilities of Brothers Winchester**

By: Eshlyn Kar

**Warning: may be some slight use of language**

**Chapter Three**

**Suspensions**

"Alright it's just like last time only this time you have to get suspended and you're not allowed to hit anyone," Sam concluded.

"Man I got into so much trouble last time; I wasn't able to sit for a month after dad got through with me."

"Yeah well I warned you, and we're leaving tonight so the school won't be able to get a hold of Dad anyway."

"Alright."

_Who can get suspended without hitting anybody within the time span of one day._

Dean wrote it in the journal.

* * *

Sam sat gloomingly in the front seat of the Impala.

"I mean seriously, how could I not get a suspension for that! I mean seriously. I freaking swore out my teacher and the principal. And they only give me a detention for the next month and a half. Pisses me off."

"Yeah well Sammy you gotta know how to get suspended," Dean said grinning from ear to ear.

"Dean I still can't believe you did that, it is so gross! I mean only you would come up with the idea of making out with a teacher in the principal's office."

"What can I say Sammy, she was a babe."

Dean: 2

Sam: 1


	4. Burping

**The Physical Impossibilities of Brothers Winchester**

By: Eshlyn Kar

**Warning: may be some slight use of language**

**Chapter Four**

**Burping Contest **

**Ps. pleaz read the note at the bottom, I NEED YOUR HELP!**

"Alright Sam, we'll have a burping contest. You get one can of Soda and that's it."

"Dean that's so immature."

"Oh come on Sammy, ever since you turned thirteen you've tried to act all dignified but I know your still the little rascal I raised you to be," Dean scoffed.

"Fine, I'll write it down."

_Who can burp the…_

"Wait so is it loudest or longest?"

"Umm…your choice Sammy boy."

"Alright," Sam continued writing.

_Who can burp the longest on only one can of Soda._

"Ready Sammy?" Dean asked after opening the can of Pepsi.

"Was born ready big brother."

"I'll go first," and with that Dean chugged the can and belched. Sam counted on his watch.

"1, 2, 3, 4, 5, 6," Sam counted out loud and Dean finished at 6.

"Okay now you have to count for me and count out loud," Sam said opening his can of Coke and chugged it down.

"1, 2, 3, 4, 5, 6, 7, 8, 9. Sam! That was disgusting! I taught you well little brother," Dean said proudly slapping Sam on the back.

"Yeah whatever Dean, you know Caleb taught both you and me how to burp," Sam countered.

"Yeah, so? I still taught you best."

"That makes no sense what so ever."

"That's what you think." Dean replied and Sam just rolled his eyes.

Dean: 2

Sam: 2

**Hey y'all, hope u liked it but i want to write one about pranks but well i don't know pranks all that well so it would help me a bunch if u could send me some ideas of pranks, original or the oldies! thanks again.**

**elyse rozema**


	5. Spitting

The Physical Impossibilities of Brothers Winchester

By: Eshlyn Kar

Warning: may be some slight use of language

Chapter Five Spitting

Contest: Who can spit the farthest.

"I wanna go first," Dean whined just as Sam was getting ready to spit. "You know you sound like your four, right?"

"Yeah whatever Sammy, you know I can still beat you up right?"

"Shut up and spit," Sam rolled his eyes and Dean went up to the line in the dust and made the appropriate sounds for spitting and let her fly.

"Hmm, not bad."

"Oh yeah, well I like to see you do better."

"Just watch me," Sam said stepping up to the line. He did the same preparations as Dean and spit.

"Ha! I told you!" Sam said as his gob went nearly nine inches farther than Dean's. "I totally taught you how to spit!"

"No you didn't, Caleb did!"

"No he didn't."

"Yes he did."

"No I did."

"You did not, even ask Dad, he'll tell ya."

"Fine tattle tale."

"What!? How does that make me a tattle tale?"

"Because I said so that's why."

"And who said you were always right?"

"Sammy it's in the book of Physical Impossibilities of Brother's Winchester, I won that month which means I am always right. And besides I'm older."

"You have to stop using that argument, it's so old!"

"You're so old."

"What? You're older than I am."

"Yeah well… you're so old."

"UH! You're impossible Dean!" Sam yelled stomping away to write his victory into the book.

"Ha, Dean you still got it, even if Sammy is winning, you're winning in your own books and that's all that matters. And I'm also an insane person talking to myself, great."

Dean 2 Sam 3


	6. Stronger

The Physical Impossibilities of Brothers Winchester

By: Eshlyn Kar

Warning: may be some slight use of language

Chapter Six Stronger

"Dean, could you please turn off that freaking television!?" Sam asked impatiently from his seat at the kitchen table.

"You snooze you loose kiddo." Dean mumbled from his position in front of the T.V.

"What does that have to do with anything? I have to finish this report and you aren't helping! So could you please just turn off the T.V."

"No."

"Dean you are such a child, turn off the television." Sam said getting up from his chair and angrily stalked towards Dean.

"No." Dean said still focused on the television.

"Dean I swear I'm going to…"

"What Sam? Beat me up? You know I'm twice as strong as you."

"Like hell you are, come on lets do this," Sam said putting up his fists.

"That's not how you test your strength, come on Sammy lets have a good old fashion arm wrestle and we'll see who's stronger." Dean got up off the couch and walked past Sam and sat at the table. Sam sat opposed to him.

"Alright Dean lets do this." Sam slammed his elbow on the table and Dean did the same. They clasped hands and got ready to arm wrestle.

"Okay on the count of three. One, two, three." Sam and Dean both pushed as hard as they could. At first it looked as if Dean was winning but slowly Sam got the upper hand. The two teenagers grunted and groaned trying to get leeway with the other. Suddenly Sam felt a sharp pain on his shinbone and let up and Dean slammed his hand onto the table.

"Booyeah!!" Dean jumped from his seat, with his hands in the air.

"You jerk, you kicked me! That's not fair!"

"Whatever Sam, you never said anything about kicking." Dean once again flopped onto the couch and turned on the television.

"Your such a jerk."

Dean 3 Sam 3


	7. Higher

The Physical Impossibilities of Brothers Winchester

By: Eshlyn Kar

Warning: may be some slight use of language

Chapter Seven Higher

"Hey Sam I bet I can climb a tree higher than you can." Dean said as he swung himself up onto a branch.

"Your on." Sam agreed as he jumped into the tree beside Dean's.

"Okay, in ten seconds we have to get as high as you can and then we'll see who got higher, alright."

"Okay. Ready, set, go!" Sam grabbed onto the branch above his head and swung himself up. He could hear Dean counting, from beside him.

"6, 7, 8, 9, 10. Stop!" Sam stopped climbing and looked over at the tree beside him, but he couldn't see Dean.

"Dean?" Sam asked looking over the tree.

"Right here Sammy," Sam finally saw Dean about ten feet higher than him.

"How did you get so high?" Sam asked mystified.

"I'm just that good!" Dean snickered, wrapping a rope around his fist and putting it into his backpack, "I'll teach you how to climb a tree sometime."

"Shutup."

Dean 4 Sam 3


	8. More Shots

More Shots

_Eshlyn Kar_

Sam grabs the tray of shots and makes his way to the table Dean had saved earlier.

"Alright Dean, we'll both drink and see who passes out first."

"Alright Sam, but don't come onto to me or nothing when your hammered cuz I'll have to put the smack down on ya." Dean smirks grabbing his shot.

"Shut up and drink." Both Dean and Sam shoot back their drinks and slam the glasses back on the table.

"Just remember dude, no argument and no excuses, who ever drinks the most wins." Dean says while grabbing his next shot.

"Whatever."

Many drinks later…

"Come on Dean, give up already, you know… you know I can, can hold more liquor than you…." Sam hiccupped.

"You would think so, seeing how friggen tall you are. Dude! You are sooooo tall!" Dean drawled taking his next shot.

"I know!! It's so awesome! But you… you're awesome, you that right man."

"Yupp, I know. " The next shot was taken.

"No I mean, your awesome, like so so awesome."

"Yeah… I'm basically Captain Awesome! Whoa, Captain Awesome!" Dean whooped and jumped up with his arms in the air. The bar was filled with laughter and someone hucked a bottle cap at Captain Awesome and Dean sat back down and took his next shot. Sam was nearly keeling over with laughter and could barely keep the shot from spewing back up.

The next shot was in both of the Winchester's hands when someone bumped into Dean and spilled his drink all over him. Dean stood up and decked the guy who had bumped him. The guy hit him back and Sam jumped up yelling, "No one hits Captain Awesome!" and decked the guy again. At that point both of the Winchesters were kicked out of the bar and a cab was called.

The next morning both boys were taking turns in the washroom, hurling and piling on the Advil.

"Dude, I totally won," Sam says looking up from the toilet.

"What filthy lies are you spewing now? No one won. We got kicked out!" Dean said brushing his teeth.

"Nope, your drink got spilled, I drank mine!"

"DUDE! That so doesn't count!"

"It so does!"

"Whatever man, I woulda wupped yer ass!"

"But you didn't."

"Due to someone else interfering."

"You said no argument, whoever drank the most won. I drank the most, I won!"

"Whatever man."

"HA! Now who's Captain Awesome!?!" Sam rolls onto the floor laughing.

"Shut up you little bitch." Dean spits into the sink.

"No man I'm not little, you said so yourself. I'm really tall."

"And I'm soo sooo awesome."

"Yeah, well I won so I guess that makes me really really awesome."

"I friggen hate you."

"Captain Awesome!"

"More like Captain dead rotting cat with maggots in it."

Sam moans and sits back up at the toilet.

"Sick."

"Haha!"

Dean 4 Sam 4


	9. Dizzy Race

Dizzy Race

Eshlyn Kar

"Okay so what you have to do is put your forehead on the bat like this and then spin around ten times. Make sure your forehead doesn't leave the bat and the bat can't leave the ground. Then you have to run to the first base and back. Whoever makes it back first wins," Dean explained the next bet to Sam.

"This is stupid," Sam complained while he set his forehead to the bat.

"Stop your complaining Betty Boop. On your mark, get set, go!" Dean and Sam ran as fast as they could in circles with their bats. Sam fell over at six but quickly got back to his feet and continued his circles. Dean finished the spinning first but keeled head first into the dirt as soon as he tried to run. Dean fell again trying to get up but on the second try finally get his feet under himself. Sam was running sideways towards middle base. Both Sam and Dean collided on first and had to pull themselves apart before running straight as possible for home base. Sam was just ahead of Dean but Dean launched himself for home and slid in just before Sam. Dean started cheering and Sam pouted but neither was aware of Castiel killing himself laughing on the sidelines. Humans could be extremely entertaining.

Dean 5 Sam 4


	10. Caz's Dare

"All right Caz, this is a human thing, we call it a dare. When I dare you to do something, you do it," Dean tried to explain to the confused Angel. The two of them were sitting in the car. Both were extremely bored on their very long car ride. Sam was sleeping in the back seat.

"Why don't you just ask me to do it, why dare me?" Castiel asked.

"Because a dare is supposed to be something you don't want to do. Like I dare you to kiss Sam, or something like that," the angel looked disgusted and shook his head fervently.

"I would not ever do that. Why would I do something I didn't want to just because you dared me to?"

"Because if you don't then if means you're a coward," Dean explained.

"I am no coward Dean Winchester, I have faced down Satan himself and didn't even quiver," Castiel said sounding quite offended.

"I know that Caz, it's just apart of the game. Now are we gonna play or not?"

"I guess I will play, if there I nothing else to do."

"Okay, I dare you to lick the window," Dean started the game with something easy.

Castiel looked like he wanted to argue but instead just did the dare.

"I get to dare you now?" Castiel asked, a grimy, salty feeling on his tongue.

"Yep."

"I dare you to slay three demons, casting them back into their unholy perdition," Castiel dared. Dean glared at him.

"I can't do that right now, you have to say something I can do in the car. Like I dare you to smell Sam's foot," Dean dared Caz. Caz looked at the foot right behind his head in disdain. He didn't care for the smell but sniffed it anyway. With a gag he turned to Dean.

"I dare you to cut off your nose," Dean looked at Caz in disbelief.

"What? No! You're not getting the game. The point of the game is to make someone do something gross, or embarrassing. Not disfiguring," Dean explained in exasperation.

"Alright, I dare you to kiss Sam," Dean looked at Caz and then back out the front window.

"I really don't like playing this game with you."

Caz 1

Dean 0


	11. Caz's Dare part II

"Hello Sam," Sam jumped, nearly crashing into the car beside him as Castiel suddenly appeared beside him. He was on his way to meet Dean a state over, where they were following a lead about God. Dean had hotwired a car and booked it over there the day before. Sam stayed and finished cleaning from their latest hunt before joining him.

"Holy crap, Cas! You just came out of nowhere," Sam said getting a hold on himself.

"I did not come from nowhere, I came from a hotel. Though far away, it is not nowhere."

"No Cas it's a figure of speech, oh, never mind. What were you doing in a hotel?"

"Looking for God of course, there was a rumor that he was there," Cas answered in his usual dead-pan manner.

"So you didn't find him then?" Sam asked.

"No." The two sat in silence in the car for a while and Sam wondered why Cas wasn't flying off.

"Was there something else?"

"Yes, I just don't want to do it," Castiel said deadpan. Sam looked at him alarmed.

"What's wrong Cas, did something happen to Dean?" Sam still looking at Cas and was suddenly kissed full on the lips. He pushed the angel off him and wiped his mouth.

"What the hell Cas!!! Why did you just kiss me?!?"

"I am no coward," the angel said refusing to meet the stunned hunters gaze. Cas disappeared in a flurry of wings, and Sam remained in the car, very confused.

One state over…

A very flustered Angel appeared before a very humored Dean.

"Did you do it?" Dean asked trying to keep the smile from his face.

"It has been done," Cas said with a wince. Dean burst into a fit of laughter, falling off his seat and holding his sides. Castiel looked quite miffed at Dean's mirth.

"My turn right?"

"Yes Cas it's your turn," turn said wiping tears from his eyes.

"I dare you to get into an airplane and fly to your next hunt."

"Oh fail."

Cas 0

Dean 0

Sam 0

(No one won that time)


	12. Caz's First Prank

Dean giggled rather childishly as he placed the shaving cream and molasses on his sleeping brother's hand.

"I don't understand your over-exuberant glee. Why is this funny?" buzz kill Cas asked, deadpan as always. Dean hushed him impatiently. He had taken it upon himself to teach Cas what it was to be human and the most important thing about humanity, he decided, was humor. Try explaining that to the most unhumourous being in existence.

He gave Cas the feather and gestured for Cas to carry out the rest of the prank. He had explained to the angel earlier about pranks and this one particular. Dean made up a plan to get his brother and explained it to the unenthusiastic Castiel.

"Why is that funny?"

"I don't know it just is," Dean explained hours earlier.

Now Cas looked rather perturbed as he grabbed the feather and walked over to the sleeping hunter. He tickled Sam's nose like Dean had told him to. At first the hunter merely scrunched his nose and moved his face away, but with silent urging from Dean, Cas kept tickling.

Instead of swatting his face with the stinky shaving cream and gooey molasses like they had planned, Sam swung his arm out sleepily, swatting Cas on the tummy. The shaving cream and molasses splattered on his nice suit with a loud smack. Cas looked so unpleased Dean couldn't help but burst out laughing. Sam jumped awake confused and stared at his laughing brother and the pissed angel.

"This is a stupid joke," Cas said looking very displeased. "This is a very nice suit, I like this suit." He nearly whined. Dean laughed harder.

"Oh don't be a poor sport!" Dean yelled as the angel disappeared.

"You think he guessed I was in on it?" Sam asked suddenly smirking.

"Nope! He had no idea!" the brothers laughed at the angel's expense and Cas watching silently from just across the veil, plotting his revenge.

Dean 1

Sam 1

Cas 0 (for now…)


End file.
